The making of a brand-new iPad magazine that's already sick of the Internet

Jim Windolf, a contributing editor and writer for Vanity Fair, was sitting in a large, multi-desk cubicle in a warren of similar cubicles in a 10th floor office on West 27th Street on a rainy afternoon, explaining his new project.

The office, a temporary space shared with a bunch of local startups and paid for by the desk, was spare, but what stood out were the stacks of books, and a big copy of the Spy magazine anthology that came out in 2006. It was his sixth day on the job, and he made several apologies for having not much specific to say about his plans. But he actually had a lot to say.

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Windolf, 48, is a recent addition to the group of people who are behind Punch!, a new iPad publication that is, for now, mostly a sparsely populated "bookshelf" of interactive games and visuals and other little graphic toys on the broad themes of contemporary politics and pop culture news. (It's free at the App Store, here.)

"The web is increasingly feeling like noise and bother," he said. "I mean I read it, all day. But I don't always feel so good afterward."

What he sees in Punch! is the possibility of creating a successor to Spy, the seminal late-'80s monthly-magazine brainchild of Kurt Andersen and Graydon Carter that was a turning point in the culture of magazine-making and reading. It was a relatively short-lived, money-losing proposition that, in the final stages of its growth, scattered its seed across Manhattan like some kind of plucked dandelion, sprouting nasty bits of yellow everywhere it landed.

"On the other hand, I used to read Spy and not feel great afterward, either," he said. "That's something people forget."

The two of us had thumbed through the Spy anthology and he had been pointing admiringly to lots of its pieces and features. We both found ourselves doing what one always does looking at that book: Wondering where the energy came from to be so enervated about the culture, to have it sprout out so easily, so messily and so perfectly on the page.

Windolf, a former editor at the Spy-inflected New York Observer (where I also worked, though not at the same time) wasn't really contradicting himself about that feeling of indigestion.

Much of the web is an endless array of little bites one after the other, a Tapas restaurant from hell. At some point you walk away from the table and pay an astronomical bill, but those little bites are still arriving at other tables, piling up in your absence, swimming in garlic and grease. It's possible that nothing you've tasted yet is as important or as good as the things now accumulating there, you think, as you make the difficult choice to walk away.

Spy was something else: A big, rich meal, served at a white tablecloth, course after course. Before long, dawdling over each plate becomes something you do in the hopes that someone will take it away, and that suddenly you'll be given a cup of coffee, or some other sign that your gluttony was near an end. And then you got it: the last page of the magazine. You wouldn't be eating again that way for a month.

Windolf pointed to a piece by Philip Weiss that appeared in the November, 1989 issue of Spy, called "Masters of the Universe Go to Camp: Inside the Bohemian Grove."

The piece clocks in at 10,000 words—hardly the stuff to down between courses of data entry or legal briefs or stock trades. But it is also spread out in the magazine over 13 pages, giving each page a very luxurious average for cartoons, photos, and sidebars.

"Spy always seemed like it was fighting the limits of what you could do with print," Windolf said.

There are lots of reasons publishers of magazines, long-form journalism and nonfiction writing and the like have hailed the coming of the iPad. The boring part of all that is whether the simple fact of the new platform allows publishers a pretense to start charging for content. The interesting part is what happens when publishers, many of whom have for some reason or another never really taken the time to develop a language for their literary ambitions on the Internet, actually begin doing so for the iPad.

Windolf brought up the early Soviet film director and theorist Sergei Eisenstein.

"In early film, someone had to invent the grammar of it," he said. "That you have a shot of someone looking to the right, and then cut to someone looking to the left, that they are looking at each other—that was invented. They had to invent the grammar of film."

Publishers' work on the internet pales in comparison, really, to those 20 years at the beginning of film when it comes to developing a web-specific storytelling grammar. And that's where Windolf, like some others before him, sees some potential.

"It's specific to the tablet, to swiping around and moving on the surface of something rather than clicking and typing," he said.

So far, there isn't much on Punch! that could really exist anywhere else.

There's Cabin Pressure, an illustration featuring a cutaway model of an airport with a plane on the nearby tarmac that comes with the sound effects of a muted airport P.A. system. You quickly gather that touching various people and things around the airport will bring up a box with a little story in it, like, say, one that makes reference pop singer Bjork's history of getting into trouble at airports. Some items have video or pictures in the box that you can touch to watch. You certainly could make this for the real internet, and have hover-states for the mouse pointer that told you where to interact. But in all likelihood nobody would, because the economy of the internet provides a strong disincentive to spend the money and development time on something like this, which audiences will often reach unintentionally.

Same with what happens when you click an item on one of the shelves that's a still-life of an old-time radio set, a raw steak, a jar of Pepto-Bismol and a scotch on the rocks. It navigates you to a page where a group of people sitting around a table, drawn by a cartoonist but with heads cut out of real photos,are drinking, yakking, eating and smoking cigars. There is quiet movement on the page: Piers Morgan blinks, Tio Salamanca rings a bellhop-bell on the arm of his wheelchair, the smoke billows from Rush Limbaugh's cigar. You know instinctively to touch the faces, which are set off simply by being photographic; an audio file plays with a recent, famous recorded rant from each.

Every publication has a tagline, and several have been trotted out for Punch!, which takes its name from the old London satire magazine founded in 1841 by British reformer Henry Mayhew and the wood-engraver and illustrator Ebenezer Landells. The original Punch was tag lined "The London Charivari," after the custom of the community rallying outside the house of someone who had breached its standards and banging loud instruments and singing rough songs to embarrass them into compliance. It was an early, and apt, metaphor for the power of magazines and illustrations to afflict the comfortable; the comforts it offers the afflicted are just the pleasures of spite.

But every publication also has a secret, a thing that they are doing in the background to organize its readership around an editorial point of view that can be repeated in daily or weekly editions forever, and that can grow.

I asked Windolf what the secret of Punch! was going to be, and he, by way of contrast, brought up the founder of Buzzfeed, Jonah Peretti.

In many ways, what Buzzfeed does is to capture the public imagination in as concise and encapsulated a way as possible; to allow readers to consume a tiny, tiny bit of zeitgeist, and quickly spit it out everywhere through their social networks. If there are viral phenomena, Buzzfeed seeks to be a sort of virus-synthesizing laboratory. And viruses feed on the tiny gaps in people's days created when one task has been crossed off a to-do list and the next one awaits. Though news has become an increasingly large part of Buzzfeed's mandate, news that requires lots of time to digest hasn't.

By contrast, Windolf said of his project, "The secret idea is it's a respite from the madness of the web, which is getting crowded."

"You use the iPad differently from how you use a computer," he said. "You're not going to come here to learn that Dick Clark died two minutes ago. This is something you read in your leisure time and not in the cracks of the work day. You downloaded the app, and you want to do something like that, you don't want to just have the same experience you could on your computer. It can maybe feel more like the Sunday paper."

IT WAS ONLY A FEW WEEKS AGO THAT A FRIEND INTRODUCED Windolf to David Bennahum, a guy I hadn't heard of by name before either. When I moved one cubicle down to talk to him, I was surprised I hadn't.

Bennahum is a natural talker. He was leaning back, all skinny limbs barely contained in a creaking Staples chair not made for leaning back in. All his gestures are expansive, the unavoidable tics that come with his quite impressive enthusiasm for talking about media, business, art, culture and politics. I was supposed to be catching up with him on some details of the business for about five minutes, and I was with him for an hour.

He told me that two years ago he looked and was surprised to learn that the name "Punch" hadn't been picked up by any magazine or digital app or website, after Punch was finally shut down for good in 2002.

Bennahum brings a certain mix of obsession and outrage to everything he talks about, including his version of the story of how he got the name.

The original Punch was discontinued in 1992, after publishing continuously for more than 150 years. Four years later, Mohamed al-Fayed, billionaire father of Dodi, paramour of Princess Diana, frustrated at the dogged coverage of his son in the British fortnightly Private Eye, bought the name and rights to Punch in order to have a platform to fight with Private Eye. Over six years of publication it was said to have lost 16 million pounds and to have registered a subscription base of 6,000 people.

The Al-Fayeds did not retain any of the rights to the name, and Bennahum grabbed it. (Subsequently, original Spy editor Graydon Carter and former New York Observer editor Peter Kaplan told Windolf they'd noticed someone grabbed it, but didn't recognize the name.)

But the origins of Punch! preceded that by more than a year, and seem to sum up the 44-year-old Bennahum's professional and intellectual wanderings over the last 22 years.

He started out writing for the founding bunch at Wired in 1994, something he described as a "wonderful ride," but also was a contributor to Lingua Franca, the now-defunct magazine of ideas and academia, and a columnist for Slate. He wrote the book Extra Life: Coming of Age in Cyberspace in 1998, that was inspired in large part by his very early tech leanings.

Bennahum started programming as a kid, and understood early on the power of the internet. He remembers that back in 1990, the year he graduated from Harvard, he was sitting with former New Republic publisher Marty Peretz and told him that "one day every house would have a fiber optic cable connected to it, and all our entertainment will come from there," a claim Peretz was skeptical of.

But in 1993, when the first web browser, Mosaic, came out, he had his St. Paul moment.

"I felt like Alice going through the looking glass," he said.

He was an ingredient in many late '90s Internet businesses, including Laurel Toby's MediaBistro (which ultimately sold for $23 million in 2007) and Dany Levy's newsletter, Daily Candy (which was sold to Bob Pittman for around $3 million in 2003 and then to Comcast for $125 million in 2008). But he had moved on by the time that money rolled in.

He also worked in advertising, at the firm Ammirati Puris Lintas, on campaigns for Dell, Unilever, U.P.S. and Lego, before co-founding an angel investment firm called New Things with Martin Puris in 2000.

But nearly three years on that side of the startup game were enough for him, especially when the Sept. 11 terrorist attacks happened.

"I thought, I can't do this anymore," he said.

He cashed in his chips and became a media activist. First, he met David Brock, and helped him make his first business plan and hire the tech team for Media Matters. Then he worked on a Washington donor collaborative called Democracy Alliance, which steered tens of millions of dollars to political projects from deep wells of political money like George Soros and the Pritzker Family.

He created and found the money for The American Independent News Network, the publishing foundation that would produce the Washington Independent and sites like it in several other states. Curiously, in his political publishing, Bennahum was always a print guy, even if many of his ideas for other kinds of business were squarely in Internet territory; Independent was a creature of the Internet.

In the 2000s, Bennahum became a devotee of Radar, the magazine invented by Maer Roshan that had several incarnations before ultimately being folded in 2008; and, also, "I got my fill of serious political writing."

He first started thinking about something different when he got a letter in the mail telling him Radar had been shut down, and that he'd be getting Star instead to fill out his subscription. Eventually, he contacted Roshan.

"Maer and I started riffing on what could be done," he said. "A week after that, the first iPad came out. I thought actually [of] a satirical weekly coming out of Washington, in print. And it sort of evolved into Punch."

"David being David, he had an iPad the first hour," Roshan later told me on the phone.

Bennahum went through the looking glass again. Here was an opportunity to take everything he knew, and everything he'd left behind as broken, and put it together. The iPad, he thought, promised a new and totally different atmosphere for design and interaction, and therefore for advertising.

So he came back to New York to start Punch! in earnest.

The iPad presented a new platform but a rarefied one, which it would take a long time for average designers, publications and creative people to learn to build apps for, like the early days of the Internet when hard-coded HTML was all that was available, before Blogger and Moveable Type and the like.

It presented a magazine-like setting, but one that could be profitable with a small, wealthy subscriber base.

And most of all, it presented an opportunity to take the news, and humor, and multimedia, and bring them together into a publication with a distinct, throaty voice. If Rupert Muroch's The Daily is USA Today for the iPad, Punch! could be its Spy.

Bennahum's interests and experience also gave him a deep goodwill account that he could dip into in exchange for equity to build the first prototype. It's not every startup that can draft Luke Hayman, a designer from Pentagram, probably the most influential print design shop in New York, to develop the logo and pages for a prototype. Or that can draft Deacon Webster, from the ad agency Walrus, who had worked with Roshan on Radar, to come up with ideas for advertising.

"We have to reinvent advertising," Bennahum said. "It's long overdue."

Bennahum showed me an interactive custom app they'd developed for the Tribeca Film Festival: A cartoon map of the city allows you to move around and touch things that relate to movies in the festival.

Most impressive was one ad vehicle still in development. A beautiful model stands in the center of a white background in her underwear; she's in black and white. Up on the left, the neat thin letters of the Calivn Klein logo are visible. Along the right are small crumpled pieces of clothing. Touch the screen and it fades into color ("like The Wizard of Oz," said Bennahum, though it made me think of the Paris fashion-show scene in The Women). Touch the pair of jeans on the upper right, and the still model comes to life in video, turns around, opens her arms. The jeans are thrown to her from "inside" the icon, she catches them and pulls them on. Touch and throw the pants back at the icon, or touch the "shirt" icon and she puts that on up top.

BUT MUCH OF WHAT MIGHT MAKE THE COMPANY work is behind the scenes. At one of the monthly New York Tech Meetups, Bennahum recruited developer Dan Wyszynski, who worked closely with him on the prototype but most importantly on a patent-pending technology to help make iPad app development simpler for other publishers.

Web articles and internet posts with wildly different requirements and styles built on top of them have been successfully turned into standardized forms in the backend. These are the things you fill out in Blogger or Moveable Type or whatever blog software you use to come up with your website. Why couldn't the same thing be done with visualizations, with small apps, with games?

A provisional patent lists Wyszynski along with Bennahum, and basically forms both a real, working "CMS," server and for this completely different kind of content. It's licensable; it's usable to create flash-apps and mini-apps for corporate clients on a custom basis by Punch! whether they live inside or independent of the Punch! app.

"Punch wouldn't be possible without this technology," Bennahum said, as he showed me the provisional patent.

He raised $2.25 million in seed money from New York investor-incubator Betaworks, as well as New Enterprise Associates, Tisch Tech Stars and privately from Daily Candy founder Dany Levy and Jason Calacanis.

These are convertible notes. He now thinks it's time for a Series A fund-raise.

After a soft launch on April 12, the final team had taken shape: Jim Windolf would be the top editor, working with Brooke Siegel; Wyszynski would stay on as Chief of Tech; Kate Elazegui (Money, New York magazine) would run the design department.

Levy is still on hand, and has the title of creative director, and works a lot with creative and marketing. Roshan is still on hand as a friend of the app and is listed on the masthead as the Founding Editor, but, Bennahum said, Roshan had done plenty of start-up work and had other projects he wanted to devote himself to.

As Roshan later put it to me, "I've been working in startups for the better part of a decade. It's always a good feeling to hand it off."

He was in overdrive with Punch! and his own website, The Fix, which focuses on the "addiction industry" and is a sort of brilliant mashup of exposes, celebrity rubbernecking and serious talk about addiction and recovery, written and consumed by people who have been there. He said he was surprised when both got funding at the same time, but that he couldn't do both. (He's writing a book now about "the addiction industry," which he characterizes as a $1 billion industry that's never really been looked at from a business point of view.)

Roshan remembers that Windolf, then at the Observer, used to play pranks on him, one of which Windolf remembered to me: Showing up for a lunch meeting with Roshan at a Greek place near Carnegie Hall, he had an intern pretend to be his personal valet. Who better to do Punch?

RIGHT NOW, THERE ARE ABOUT A DOZEN "OBJECTS" on the three shelves of Punch!. Windolf said that the goal is to bring in new content daily, though they're moving at a deliberate pace right now. When I spoke to him he hadn't yet finalized any assignments, but he was willing to say a bit about what he was looking for.

For one thing, he agreed that a shelf of toys is sort of just a shelf of toys. Grownups also want books, and films and TV shows in their entertainment and informational toolkits.

That night, Windolf was heading to the Upright Citizens Brigade Theater, the beginning of a mission to forge a relationship between Punch! and the New York comedy circuit analogous to the way the website Funny or Die! seems to have the Los Angeles scene on speed-dial.

Also, looking at all the toys, Windolf pointed out, "Each one of these things takes a long time to make."

"We're working on having some simpler things that can go up more frequently," he said.

Video shorts and photoessays, too. The quiz is one example. Creating more "departments" like that that require some editorial work on a regular basis but not heavy doses of new programming and design will be a part of it.

And so, of course, will text.

"Funny reported pieces, skeptical reported pieces, maybe they don't make you laugh out loud but are skeptical in some way," Windolf said, all centered around current politics, pop culture, tech and media.

"We could have a piece that scrolls endlessly, that isn't about pages, and that seamlessly introduces video, and interactive, and visualizations and photography," much as the apps are elsewhere but launching out of and into stories that readers can sink their eyes into and read.

"We don't have to do all journalism," Windolf said. "Vice does video comedy shorts. It could end up ultimately having its own channel, too."

But that is the easy stuff. The hard part will be the Eisensteinian rigor. How can Windolf publish his own "Bohemian Grove" in a way that could never have been done at Spy?

Windolf didn't really have any answers on Day 6 of the job. But it's not hard to see why Bennahum hired him.

While working at Vanity Fair, Windolf and his pal Peter Stevenson, both Observer alumni, found themselves constantly imitating and thinking about their old boss and friend Peter Kaplan. Twitter had arrived in the mainstream, but it still seemed a mysterious if not ridiculous sort of forum.

Soon, the widely revered but by no means world-famous Kaplan found himself a Twitter celebrity, as Windolf and Stevenson built several Twitter "storytelling" accounts, each told from different characters that represented different caricatured facets of Kaplan's distinct personality. There was @crankykaplan, @realkaplan, @wisekaplan; a quite sophisticated recent entry is a "premium" kaplan account, which nobody is a member of.

[Wise Kaplan], not long ago, leapt from his office window. His dive, a lovely free fall down the Condé Nast building, defied physics, played off Twitter's frame-by-frame short form, and perfectly distilled the Kaplans' resilience to the perils of their madcap world:

9:05:26 p.m.: Standing on windowsill, telling secretary I'll jump if she leaves me now. She says I don't have the guts and the window doesn't even op

9:05:59 p.m.: Awning.

9:06:27 p.m.: Nother awning.

9:06:43 p.m.: Yellow Cab™ roof.

9:11:23 p.m.: Whatta town.

It's proof that Windolf has passed the Eisenstein test before. Why not again?